Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Rome
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, a water park, and an in-room coffeemaker. Popular attractions Belgrade Lakes Golf ...
Cozy Long Pond Cottage: private mooring & shared dock
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Manchester
Book a stay at this golf vacation home in Manchester. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Cobbosseecontee Lake and Augusta Country ...
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Augusta
Stay at this vacation home in Augusta. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Old Fort Western and Augusta ...
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
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Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

Readfield
Stay at this vacation home in Readfield. Enjoy parking (surcharge), a garden, and patios. Popular attractions Town Beach and Maranacook Lake are located ...
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Lakefront, Stunning Home only 30 min to Sugarloaf!

Lakefront, Stunning Home only 30 min to Sugarloaf!

Strong
Stay at this vacation home in Strong. Enjoy free WiFi, a garden, and patios. Popular attraction Porter Lake is located nearby.
Lakefront, Stunning Home only 30 min to Sugarloaf!
Private and Calming Waterfront to the Rescue!

Private and Calming Waterfront to the Rescue!

Augusta
Stay at this vacation home in Augusta. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Viles Arboretum and Pine Tree State Arboretum ...
Private and Calming Waterfront to the Rescue!
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Spacious Country Home w/ Hot Tub, near Colby/Thomas

Sidney
Stay at this vacation home in Augusta. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attraction Natanis Golf Course ...
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH

Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH

New Vineyard
Stay at this vacation home in New Vineyard. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attraction Porter Lake is located nearby.
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH
Lake House Wooded Vacation Retreat and Nature Escape

Lake House Wooded Vacation Retreat and Nature Escape

Farmington
Stay at this vacation home in Farmington. Enjoy a fitness center, patios, and an in-room coffeemaker. Popular attractions UMF Art Gallery and Richardson Tract ...
Lake House Wooded Vacation Retreat and Nature Escape
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oakland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oakland vacation homes are the perfect way for you to wing it.

Holiday houses in Oakland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oakland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oakland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oakland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oakland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oakland Holiday Homes essential information

Accommodation
120 Holiday Homes
Lowest Price
NZ$444
Highest Price
NZ$444
Popular accommodation
Cozy Long Pond Cottage: private mooring & shared dock, Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly, Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak, Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK, Lakefront, Stunning Home only 30 min to Sugarloaf!, Private and Calming Waterfront to the Rescue!, Spacious Country Home w/ Hot Tub, near Colby/Thomas, Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH, Lake House Wooded Vacation Retreat and Nature Escape

Top trending hotels in Oakland

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Oakland
Stay at this cabin in Oakland. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Tree Spirits and Belgrade Lakes Chain are located ...
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Rome
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, a water park, and an in-room coffeemaker. Popular attractions Belgrade Lakes Golf ...
Cozy Long Pond Cottage: private mooring & shared dock
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland
The price is NZ$444 per night from 29 Dec to 30 Dec
NZ$444
includes taxes & fees
29 Dec - 30 Dec
Stay at this apartment in Oakland. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Belgrade Lakes Chain and Tree Spirits are located ...
Central Maine Apartment offering 4 Seasons of Fun.
Save an average of 15% on thousands of hotels when you're signed in
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Rome
Stay at this vacation home in Oakland. Enjoy a garden, a picnic area, and patios. Popular attractions Belgrade Lakes Golf and Belgrade Lakes Chain are located ...
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Don't see what you're looking for?
See all available properties in Oakland
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.